Benzyl chloroformate → 4(R)-Benzyloxycarbonylamino-2,3,4,5-tetrahydro-1H-2-benzazepin-3-one

HRID 1078157Notes

Reaction equation

HRID 1078157 reaction equation
[NH2:1][C@@H:2]1[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[CH2:5][NH:4][C:3]1=[O:13].C(=O)([O-])[O-].[K+].[K+].Cl[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22]>O1CCCC1.CCOCC>[CH2:24]([O:23][C:21]([NH:1][C@@H:2]1[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[CH2:5][NH:4][C:3]1=[O:13])=[O:22])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 22864416(R)-4-Amino-4,5-dihydro-1H-benzo[c]azepin-3(2H)-one

Product 1

HCID 228644254(R)-Benzyloxycarbonylamino-2,3,4,5-tetrahydro-1H-2-benzazepin-3-oneYield 96%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 210 mg (1.19 mmol) of 4(R)-amino-2,3,4,5-tetrahydro-1H-2-benzazepin-3-one in 5 mL of tetrahydrofuran was treated with 5 mL of 10% aqueous potassium carbonate followed by 0.20 mL (0.24 g, 1.3 mmol, 1.1 eq) of 95% benzyl chloroformate. The mixture was stirred vigorously at room temperature for 6 hours then diluted with 20 mL of ether and the mixture transferred to a separatory funnel. The lower aqueous layer was removed and washed with several portions of ether. The combined ether washes and ether layer were washed, with saturated aqueous sodium chloride, dried over magnesium sulfate, filtered and solvents removed under vacuum to give 365 mg (1.14 mmol, 96%) of the product. 1H NMR (400 MHz, CDCl3): δ3.08 (dd; 12, 16 Hz; 1H), 3.27 (dd; 7, 16 Hz; 1H), 4.06 (d, 16 Hz, 1H), 4.75 (d, 16 Hz, 1H), 5.00 (dd; 7, 12 Hz; 1H), 5.12 (s, 2H), 7.1-7.4 (m, 9H).

Workup

  1. customthe mixture transferred to a separatory funnel
  2. customThe lower aqueous layer was removed
  3. washwashed with several portions of ether
  4. washThe combined ether washes and ether layer were washed, with saturated aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customsolvents removed under vacuum

Sources & evidence

ORD record
ord-5d1fa5d7f3af4435bb69ce5695ae3e65
Source dataset
uspto-grants-1996_08
Patent number
US05545735

Reaction notes

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